Bromocyclopentane → 1-Cyclopentyloxy-2-methoxy-5-nitrobenzene

HRID 2230997Notes

Reaction equation

HRID 2230997 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].[CH:13]1(Br)[CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH:13]1([O:12][C:4]2[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 113907411-Cyclopentyloxy-2-methoxy-5-nitrobenzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-methoxy-5-nitrophenol (4.86 g), cyclopentyl bromide (3.4 ml) and potassium carbonate (4.8 g) in N,N-dimethylformamide (50 ml) was stirred at 50° C. for 3 hours. Then the mixture was poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 3-cyclopentyloxy-4-methoxy-1-nitrobenzene (5.05 g).

Workup

  1. customThe organic phase was separated
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-a2333078922e441096099ec0aa511ca9
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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